


Game On

by Winchest09



Category: Supernatural
Genre: Dean Winchester Smut, F/M, Fingerfucking, Masturbation, Oral Sex, Sex, Shameless Smut, Smut, Vaginal Fingering, Vaginal Sex
Language: English
Status: Completed
Published: 2019-02-27
Updated: 2019-02-27
Packaged: 2019-11-06 16:48:50
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,960
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17943524
Author URL: https://archiveofourown.org/users/Winchest09/pseuds/Winchest09
Summary: You could hustle anyone at a game of pool, managing to win anyone who wanted to compete against you. Then Dean Winchester comes along and wants to bet more than just money…





	Game On

Dean entered the small town bar for the fourth night in a row, he’d just finished a ghoul case with Sam and he needed to let of some steam. He headed to the bar and ordered himself a beer before looking around. He was looking for someone in particular. Paying for his drink, he picked up his bottle and rounded the end of the bar to see you standing there, pool cue in one hand and a wad of cash in the other. A group of disappointed men surrounded you.

He met you three nights ago, fleecing money from any customer who was willing to go up against you. He was immediately captivated by you and asked you for a game, purposely losing each time against you just so he had an excuse for a rematch the following night.

He took you in as he walked over to you. Tight blue jeans showing the curves of your ass and a white blouse buttoned halfway down before being tied at the waist, showing off your stomach. His mouth watered at the sight.

“Fancy a round” Dean questioned as your Y/E/C eyes met his.

Your smirked, leaning your hands on your cue “I’ve beaten your ass the past three nights Dean, not tired of losing yet?” You teased.

Dean scoffed, waving his bottle around “To you? Never” He smiled a cocky smile “Although, I suggest changing the stakes tonight”

You looked Dean up and down, raising your eyebrows slightly “Go on”

“I bet myself” He said confidently, shrugging off his jacket.

You shook your head, disbelief in what you heard “What?”

“You win, you can do whatever you like with me. Take my money, take my body, you name it” Dean smirked, walking closer to you. You had to admit, the thought of having Dean any way you wanted him made your panties a little damp. You’d thought of him in between your legs every night since you had met him.

His lips came close to your ear, his beer bottle still in hand “I win…I get you” He hushed into your ear, his breath making your skin tingle. You watched as he walked back to the other side of the pool table, drinking from his beer.

You tried to play it off, scoffing “What’s in that bottle? Delusion?”

Dean placed his beer bottle down on the edge of the table before leaning on both of his hands “You afraid you’re gonna lose Y/N?”

There he was, standing there looking smug and it stirred something deep inside you. You’d beaten him three nights in a row, how was tonight going to be any different? You thought about having him at your mercy, doing what you were telling him to do, being in control of him. You bit your lip at the thought, squeezing you thighs together discreetly. Once you won, you’d grab him by the shirt and take him to the cellar where you’d fuck him senseless.

Looking him dead in the eye, you answered confidently “You’re so on Winchester”

He offered the break of the balls to you but you declined, wanting him to at least have a chance against you. Boy, what a mistake you made. You watched as Dean expertly pocketed every single one of his balls after he broke, you didn’t even get to have your go. It was only then you realised that this handsome man had been playing you all along.

You looked up into his green eyes and saw the smug smile on his face “Shit” You whispered, your insides already quivering at what was going to be in store for you.

Grabbing his jacket, he finished his beer before he walked over to you and took the cue from your hands. He placed his hand on the small of your back and began to lead you out of the bar. You tried so hard to hide the smile from your lips but you couldn’t. Dean guided you to his impala and held open the passenger door for you. Sliding in, you felt your pussy throb at what was to come. The smell of Dean that lingered in the car already intoxicating you.

As Dean slid behind the wheel, he looked over to you as he turned on the engine “Where too sweetheart?”

You held his gaze “My place” You muttered before going on to direct Dean to your house.

You felt lucky that it was only a ten minute drive from the bar as you couldn’t help but keep looking over at Dean as he kept his eyes on the road. He gave you no clue as to what was going to happen but you had a pretty good idea. It took all the self-control you had in you to not pull his dick out as he was driving and taste him.

Pulling up, Dean was quick to follow you to your door. As soon as it was opened, Dean was on you. His lips attacking your neck from behind as he firmly held onto your hips, ensuring you felt his excitement as you stumbled through the doorway. You hardly had a chance to shut the door and take your shoes off before he turned you around in his arms and slammed you up against the hard wood. His large hands encased your own as he pinned them above your head, you felt his breath fanning across your skin as he placed kisses just below your ear before following your jaw line.

You bit your bottom lip as you tried to squeeze your legs together, trying to ease the ache between your legs but something solid was blocking your attempt. Dean had separated your legs with his powerful thigh, applying pressure to keep you in place, so you grinded against it. You let a tiny moan escape as you felt a jolt of pressure course through you. A low chuckle rumbled in Dean’s chest “Eager sweetheart?”

“You have no idea” You answered breathlessly as you concentrated on Dean’s free hand trailing against your bare stomach. His fingers feeling feather light against your skin, leaving a burning trail behind.

Dean smiled into his kisses as he continued down your neck to the base of your throat, sucking and trailing the tip of his tongue lower to the valley of your breasts that were heaving with each breath you took. You’d never felt so hot in all of your life. Your skin was erupting with goose bumps due to the pleasure this man was giving you with just his mouth. You shuddered in anticipation to think of what else he could be capable of.

With his free hand he undid the knot at the bottom of your blouse as he captured your lips in a searing kiss, his fingers then making quick work of the buttons on your top. He had to let go of your hands above your head and as soon as they were free, you ran your hands through his hair and lightly scraped the hair at the back of his neck.

Dean ran his tongue along the bottom of your lip before you allowed him to slide it into your mouth, moaning into the kiss. You could feel your slick coating your panties, your body reacting to the man whose hands were all over your front. He started to get impatient with the buttons on your blouse, ripping the last few off to get access to your skin underneath. You gasped at his movement when his hands immediately found your skin, sliding around from your hips to the small of your back, pulling you impossibly closer to him. You slowed the kiss before capturing his bottom lip, sucking and nibbling as you pulled back, arching you back to give him a better view of your breasts. Dean’s eyes were half lidded with pleasure and once you let go of his lip, he looked down.

“Fuck” Dean whispered gruffly, looking down at your heaving breasts dressed delicately in a white laced bra, his forehead resting on yours. He knew he wanted you the first time he saw you a couple of nights ago, he’d thought about this moment each night since then but seeing you like this? He couldn’t even compare it to his thoughts. You were as hot as hell and his cock agreed with his thoughts.

His dick was straining against his jeans as the thoughts of everything he was going to do to you flashed through his mind. He slid his hands down to your ass and squeezed it, ensuring he had a good handful before his hands travelled further down your thighs. He gripped tight and encouraged you to jump, your legs instinctively going around his waist before your lips attacked his once more. You felt his bulge and the excitement shot straight through you into your core. You needed him. Your legs tightened around him, trying to gain as much friction as possible as you worked your mouth on his.

“Bedroom?” Dean mumbled against your lips, in between your heated kisses. Turning you around, carrying you towards the stairs.

You ran your nails through his hair, pressing gently into his scalp before resting them on the back of his neck “Upstairs, first door on the right”

Dean wasted no time in carrying you up the stairs, one hand blindly reaching for the door handle as his other one held you firmly in place against his body. You could feel the heat through his shirt and you couldn’t wait to run your hands up and down his clearly chiselled chest. Pushing through the now open door, the green eyed man placed you down softly on your bed, his lips never leaving yours. His tongue was dominating your mouth as his now free hands pulled your shirt off your body, throwing it behind him. In turn, you began pulling at his flannel, eagerly wanting it off him. With a quick smile, he pulled it off, his shirt underneath coming off next as he broke the kiss. Your mouth watered at the sight of his bare torso and the tattoo that was inked in his skin.

You reached forward to run your hands flat across his chest and you bit your lip when you felt him tense a little under your touch. You looked at him from under your lashes with lust filled eyes and you saw how Dean’s once bright green orbs had become dark. He wanted you, and you wanted him just as much.

You leant back onto your elbows, never breaking eye contact with him as you spread your legs a little wider. You open invitation for him to do whatever he wanted. He lunged at you, excitement and impatience rolled into one. His plump, kiss swollen lips once again connected with yours. He continued attacking you and your skin with kisses, leaving your mouth to trail kisses down towards your chest.

He pulled downwards on your bra, pulling your breasts free and your nipples reacted instantly. Groaning at the sight, Dean wasted no time in licking and sucking at them in turn. You threw your head back at the feeling, shocks being sent straight to your centre. God you wanted to touch him, you wanted to wrap your mouth around his hard cock and taste him but right now, Dean was calling all the shots.

He continued to knead at your breasts as he peppered kisses down your stomach to the line just above where your jeans were resting. He trailed his tongue from one side of your lower abdomen to the other as his hands undid your button and zipper. He looked up at you from under his lashes and smirked as he began to wiggle your jeans and panties down at the same time. The moment your pussy was bare to him, he sucked in a breath. He’d never seen something so perfect, your slick glistening in what little light there was.

You didn’t even have time to react, Dean pushed your thighs apart and ran his tongue through your wet folds. You shuddered in pleasure and Dean’s strong hands held you in place, one of them holding your lower stomach, pinning you down. 

Your hands grasped at the sheets underneath you as Dean worshipped your pussy with his mouth. His licked from your opening to your bud, sucking and kissing, earning noises from you that you’ve never made before. Dean grunted hearing you and became relentless with his technique, with his free hand, he spread your folds and flicked his tongue over your swollen clit. You were panting, moaning, screaming. Dean was toe tingling, leg numbingly good with his mouth and you knew you were going to cum in less than a minute.

He moved his hand and fingered at your entrance, teasing your hole. You whimpered, wanting him inside you. As if he could read your mind, he curled his fingers inside you, tickling and pressing gently at you core and you gasped, arching against the bed.

“D-dean” You stuttered, feeling the familiar pleasurable feeling bubbling in your core “I’m gon-gonna”

“Mhm” Dean growled, wanting to bring you to your ecstasy “You taste so good” He mumbled against your folds, the vibrations of his deep voice against your pussy sending you over the edge. You gripped tightly at the sheets, your eyes squeezed shut as you came all over Dean’s mouth, something Dean was clearly enjoying as he lapped at your juices.

As you came down from your high, you looked down to see Dean with your slick covering his mouth and chin. You pulled at him and encouraged him above you. Kissing his swollen lips, you made quick work of his jeans, pushing them down as far as you could get them. He grinned into you before he stripped himself of his clothes.

You couldn’t help but look down at his dick. His long, thick dick with a perfect pink head covered in pre cum. You bit your lip, you had never seen anything like it before in your life. Before you could lean in to taste him, Dean pushed you back towards the mattress as he pumped his dick in his hands. Stroking himself, he settled between your legs, guiding himself to you slick entrance.

You were panting, exhilaration running through your veins as you waited for Dean to stretch and fill you. He looked into your hazy post orgasm eyes and in one fluid swift motion, he buried his length inside you. Your chest heaved with the breath you took at the feeling, the burn you felt, how full you felt, it was more than you ever imagined.

You wrapped your legs around his waist, your heels digging into his bare buttocks as you gyrated your hips against him. You needed him to move so you moved for him. Dean growled low in your ear and it made your pussy clench, the sound making you quiver. He slowly withdrew himself before thrusting back into you in a swift, quick motion. You gasped before whimpering with pleasure as Dean began to thrust into you over and over again, sucking and biting at your neck. The sound of skin slapping skin echoed around your room and you knew this was going to be one of the best nights of your life.

You needed more of him, you needed him deeper. You wrapped your arms around his neck, placing your lips close to his ear, kissing the skin there. You encouraged him to roll over, you needed to be in control, and you wanted all of him. Dean tucked his arms under your frame and rolled with you, his dick never leaving you, his thrusts never stopping. You squealed at the feeling, his pubic bone pressing against your clit.

Once on top, you looked down at Dean with a smug smile on your face as you rotated your hips. You saw how his eyes rolled back with pleasure, his hands reaching out to grab at your breasts. You arched yourself back, your hands playing with his balls and you almost felt him buck beneath you. Throwing your head back, you started to ride him, ensuring you had taken him all the way to the hilt. Bouncing above him, you screamed as he hit your spot over and over again. It wasn’t long before your movements started to shudder with an impending orgasm, your second orgasm. Dean moaned at the sight of you, the low growl emitted from his throat as he started to meet your thrusts.

He grabbed at your hips, his fingers digging into your skin as he pounded into you with everything he had. He brought his hands up to the bottom of your back, forcing your body downwards onto him. You screamed as the new angle allowed him to feel even deeper than he was before. Your breasts grazed his chest, the sensation shooting through your nipples and straight to your pussy. Your second orgasm took over your body, your toes curling, your pussy pulsing as it milked Dean’s cock. An animalistic sound left Dean’s throat at the feeling and with two more thrusts, Dean coated your insides with his cum, his dick pulsing and he threw his head back at the feeling.

You collapsed on top of him, breathing heavily. You were pretty sure you were seeing spots and you were certain you couldn’t feel your toes. Dean gently rolled you off him, searing your lips in a passionate kiss as he leant over you.

A smirk evident on his face, he mumbled against your lips “I certainly potted myself a winner tonight”

“Ready for round two?” You retaliated

Dean just chuckled lowly “Game on”

**Author's Note:**

> Hope you guys enjoyed!
> 
> Find me on Tumblr too: Winchest09


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